Chester Holidays from £783

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    Save up to £335 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

Your Chester Holiday

The best way to experience this vibrant city is with a custom-made Chester holiday package. Stay in the neighbourhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. Essex Steam Train, Goodspeed Opera House and Essex Island Marina are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect holiday to Chester now.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
29 Sept - 6 Oct
found 5 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
8.2/10 Very Good! (622 reviews)
Everything was perfect!

Reviewed on 27 Jul 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
29 Sept - 6 Oct
found 5 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Pillows are horrible.

Reviewed on 9 Aug 2025

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
per person
29 Sept - 6 Oct
found 5 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
9/10 Wonderful! (1,004 reviews)
Always enjoy staying at this property as it close to the freeway and have in close proximity to restaurants.

Reviewed on 5 Aug 2025

Comfort Inn & Suites East Hartford - Hartford

Comfort Inn & Suites East Hartford - Hartford

2.5 out of 5
per person
29 Sept - 6 Oct
found 5 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
7.6/10 Good! (1,001 reviews)
The property was decent. There was a dirty tub with a ring around it. Good thing my girlfriend and I brought cleaning products. There are no microwaves In the rooms. The beds are super soft which and be a plus or a minus for some people. They have good standard hotel breakfast.

Reviewed on 6 Aug 2025

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
29 Sept - 6 Oct
found 5 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
9/10 Wonderful! (1,003 reviews)
Spacious and clean. Staff was kind.

Reviewed on 3 Aug 2025

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
1,550
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park

Top hotels in Chester

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich, New London Turnpike, Montville, CT
Fully refundableReserve now, pay when you stay
The price is £109 per night from 27 Aug to 28 Aug
£109
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (2,494 reviews)
"Great clean hotel room with 3 minute drive to casino. Free breakfast was really good. Staff was great"

Reviewed on 7 Aug 2025

Hyatt Place Uncasville - Casino Area
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Fully refundableReserve now, pay when you stay
The price is £172 per night from 2 Sept to 3 Sept
£172
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,950 reviews)
"Such a well-run establishment. From check-in to casual restaurants to high end dining, it's just so customer friendly."

Reviewed on 6 Aug 2025

Mohegan Sun
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

3 out of 5
10 Laura Blvd, Norwich, CT
Fully refundable
The price is £80 per night from 18 Aug to 19 Aug
£80
18 Aug - 19 Aug
includes taxes & fees
7.4/10 Good! (1,002 reviews)
"Friendly staff"

Reviewed on 7 Aug 2025

Holiday Inn Norwich by IHG
See all 1,061 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chester travel package cost?
Maybe less than you imagined — from a low £783, actually! By bundling flights, hotels and car rentals into a custom-built package, your trip to Chester is only clicks away.
If I'm not able to travel, can I cancel my Chester travel package?
You can. We totally understand that even the best-laid plans can fail, so we're here to help if you have to make changes to your Chester travel package. It may be possible to cancel or amend your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Chester?
Combine your bookings with Expedia to save big on your next trip. With over 550 air carriers and 1,000,000 properties across the globe, your Chester travel package can be tailored exactly to suit your budget. With all that extra money, why not include one or more interesting tours and activities? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Chester is much closer than you thought!
Does Expedia offer Book Now, Pay Later Chester holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Pressing the "book now" button is easier with this option. Just put down a small deposit on your booking and then start working on your travel itinerary.

Where should I stay in Chester?
With loads to explore in Chester, we suggest you stay near its attractions. Norma Terris Theatre, Chester Creek Marina and Plattwood Park are some good ones to add to your itinerary.
What are the top hotels in Chester?
Saybrook Point Resort & Marina and Pier Blue Inn Old Saybrook - Essex are among the most popular hotels in Chester. Why not check out the amenities and facilities at each and then make a decision?
How far in advance should I book my Chester holiday?
Search Expedia to compare international flights as soon as you know your travel dates. You can generally purchase a ticket up to a year prior to departure. If you can't find your preferred air carrier, or you're booking late, fear not. Cheap tickets to Chester sometimes appear a few weeks before the date of departure.
What does an Expedia Chester travel package include?
From hotels and flights to rental cars, Expedia can help you put together a Chester package that's ideal for you. Heading away for a few weeks? Check out a rental car, flight and hotel bundle. If you're taking a short break, a flight and hotel deal may suit you better. Experiences can also be added once you've made your booking. Our packages make it a breeze to save and plan.
What should I know before booking a Chester travel package?
Tailor deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we've got everything you need to plan your getaway. You'll save a packet just for bundling your bookings. Whether you're going on a snow and ski adventure or drinking cocktails on a beach, your ideal getaway is only clicks away.
Can I choose my airline with a Chester Expedia travel package?
Yes, so take your pick! We have access to over 550 airlines around the world, so you can design your Chester getaway according to your style and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.